DE269213C - - Google Patents

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.- M 269213 ■ - 'CLASS 22 a. GROUP

FARBENFABRIKEN vorm. FRIEDR. BAYER & CO. in LEVERKUSEN β. COLOGNE.

Process for the preparation of azo dyes. Patented in the German Empire on November 6, 1912.

It has been found that by coupling diazotized aminobenzoylamines Constitution:

-CO-C ₆ H ^ NH ₂

(in which R and .R _{1 can} mean both aromatic radicals, or R can mean an aromatic radical, R ₁ can mean an aliphatic radical) with azo dye components such as pyrazolone sulfonic acids, methylketol sulfonic acids, a- and ß-naphthol sulfonic acids, acidylperiaminonaphthol sulfonic acids, etc. new and valuable dyes are created that Dye wool in an acid bath in lightfast, greenish yellow to blue-red shades.

The aminobenzoylamine bases mentioned, derivatives of secondary amines, have not yet been described in the literature.
The nitrobenzoylamines, their homologues and substitution products, such as. B. Nitrotoluyldialkylämine, Nitroanisoyldialkylamine, can be easily z. B. obtained from nitrobenzoyl, nitrotoluyl or nitroanisoyl chloride with secondary amines,

z. B. ethylaniline, diphenylarhin, carbazole, ethyl-a-naphthylamine, etc. In the reaction the CO group intervenes in the imino group; subsequent reduction gives the associated aminobenzoylamines in good yields, which form water-soluble salts, the weakly acidic solutions of which dissociate with plenty of water. '

Example 1.

23 parts of p-aminobenzoylethyl-a-naphthylamine are mixed with hydrochloric acid (20 parts) of 19 ⁰ Be. and 5 parts of nitrite diazotized. 20.5 parts of pyrazolone monosulfonic acid are then dissolved in 300 parts of water with the addition of 10 parts of 40 percent sodium hydroxide solution. 25 parts of solid soda and enough ice are added to this solution to reach a temperature of 0 °. The diazo compound is then allowed to flow slowly into the alkaline solution of the pyrazolone sulfonic acid. The precipitating dye is pressed off. After drying, it is a yellow powder which dissolves in water with a greenish yellow color and dyes wool in an acidic bath, leveling out well in pure yellow shades of excellent lightfastness and good millfastness. Before the dyes from p-aminobenzoyl-a-naphthylamine, it is distinguished by its better flexing fastness.

■ ο · · 1

Example 2. _

27 parts of p-aminobenzoyldiphenylamine sulfate are with 24 parts of sulfuric acid, from 40 ° Be. and 5 parts of nitrite diazotized. The diazo compound is slowly added to a solution of 16 parts of methyl ketol sulfonic acid in 300 Parts of water previously mixed with 10 parts of sulfuric acid at 40 ° Be. is acidified, come in. The one after stirring for several hours

The yellow dye that has deposited is squeezed out under acidic conditions and kneaded with 30 parts of solid soda and dried. After drying, it is a yellow-brown powder that dissolves in water dissolves with yellow color and dyes wool in very clear yellow nuances.

Example 3.

27 parts of m-aminobenzoyldiphenylamine sulfate are with 24 parts of sulfuric acid of 40 ° Be. and 5 parts of nitrite diazotized. 20 parts of croceic acid (2-Naphthol-8-sulfonic acid) in 300 parts of water with the addition of 30 parts solid soda dissolved. Throw in ice to cool to 0 °. Then you let them Slowly run in the diazo solution of the aminobenzoyldiphenylamine. The precipitating dye is pressed off alkaline. After drying, it is an orange powder that dissolves yellow-red in water and wool in very pure orange tones of very good lightfastness and good whale fastness.

Example 4.

24 parts of p-Aminoanisoyldiphenylamin with 20 parts of hydrochloric acid 19 ° Be. and 5 parts Diazotized nitrite. 21.5 parts of i-naphtol-4-sulfosaures Sodium is brought into solution with 300 parts of water and 25 parts of solid soda and cooled to 0 ° by throwing in ice. The diazo solution of the p-aminoanisoyldiphenylamine is then left run in slowly. The precipitated dye is salted out and pressed under alkaline conditions. He's after drying j a red powder and dyes wool in very lightfast, scarlet-red tones in a very equalizing manner at.

Example 5.

18 parts of p-aminobenzoylethylphenylamine be with 20 parts of hydrochloric acid 19 ° Be. and 5 parts of nitrite diazotized. 45 parts of i-benzoylamino-8-naphtol-4 · 6-disulfonic acid K is then added with 400 parts of water and 25 parts Solid soda brought into solution and cooled to 0 ° with ice. The diazo compound is now left of the p-aminobenzoylethylamine slowly run in. The fancy blue-red one The dye is pressed under alkaline conditions. After drying it is a brownish red powder, which dissolves in water with a blue-red color. He dyes wool clear in an acid bath bluish red shades of high lightfastness and good millfastness.

Claims (1)

Patent claim: Process for the representation of azo color 'Substances, consisting in the fact that one diazotized aminobenzoylamines of the formula ) Ν —CO-C ₆ H ₄ -NH ₂ (in which R and R _{1 can} both mean aromatic radicals, or R an aromatic radical, R ₁ an aliphatic radical) couples with azo dye components.